


Got That Red Dress On Tonight

by MrSkost



Category: Batman (Comics)
Genre: Alternate Universe - Canon Divergence, Crossdressing, Crossdressing Tim, First Kiss, Haven’t decided if they get together yet, M/M, Probably will but don’t get yer hopes up, Steph talked him into it, Undercover, no betas we die like men
Language: English
Status: In-Progress
Published: 2019-07-31
Updated: 2019-07-31
Packaged: 2020-07-27 16:14:27
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,352
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20048893
Author URL: https://archiveofourown.org/users/MrSkost/pseuds/MrSkost
Summary: Tim blinked at Stephanie.“You want me to do what?”Steph sighed. “C’mon Tim it’ll be easy. All you need to do is go to Brucie’s Gala and pretend to be a woman!”When Tim agreed to dress up for the Gala he did not expect draw much attention especially from the formerly dead man who hated him, and especially when that attention is not founded on anger.OR Jason hits on Tim cuz he looks like a chick!





	Got That Red Dress On Tonight

**Author's Note:**

> First fic on here so bear with me. I except constructive criticism just please don’t be mean! And comments and kudos are greatly appreciated!

Tim blinked at Stephanie. 

“You want me to do what?”

Steph sighed. “C’mon Tim it’ll be easy. All you need to do is go to Brucie’s Gala and pretend to be a woman so you can get information out of Mr. Sinclair.”

“But why me?” Tim was not enjoying the thought of spending a night in heels and a dress flirting with some douchey old councilman.

“I’d do it myself but Bruce has me on patrol that night and I doubt I could slip away long enough to work the info out of him.” Steph explained. “I would have recruited Barbara but she is too recognizable and Cass isn’t the best people person around. Plus I think you could pull off a dress.”

Steph was bouncing in anticipation waiting for Tim to give a definite answer. Tim looked at her and crumbled under her pleading face.

“Fine.” He grumbled, agreeing reluctantly. 

“Yes!” Steph pumped her fists in the air. 

“Alright now we have got to go shopping!”

“Wait what,” Tim held up his hands in a ‘slowdown’ motion. “I did not agree to shopping.”

“Not actual shopping just going through my clothes and makeup to find stuff for you to wear.”

“Oh,” Tim said relieved. “Okay then, let’s go shopping.”

Going through Steph’s closet they were able to find Tim a sleek red dress and matching heels. Tim’s only complaints were the slit in the dress which ran from the bottom of the ankle length dress to his mid thigh. As well as the heels being close to six inches tall. He was going to be in a lot of pain the day after.

“So Steph, when is this Gala?” Tim asked as they were going through Steph’s makeup to find foundation pale enough for Tim.

“8.” Steph focused on going through her eyeshadow and only gave a short answer.

“What do you mean 8?” Tim asked confused. Was it in eight days? Was it on the eighth?

“What do you mean? It starts at 8.”Steph stopped searching to look up at Tim.

“Today?” Tim asked incredulously.

“Yeah?” Steph now looked confused.

“Oh okay. I just thought it was like any other day except for today but that’s okay.” Tim was not mentally prepared to be hit on today but he’d get over it.

“Is there a problem with today?” Steph looked worried.

“No no it’s fine, promise.” Tim assured.

“Okay you sure?” Steph had stopped rummaging through the makeup kit completely to watch Tim.

“Yeah I’m sure.”

“Alright then let’s get you all dolled up!”

Getting ready had taken Tim infinitely longer than he had expected. Putting on the dress and shoes were as easy as planned but makeup and styling the shoulder length black wig Steph gave him? It took hours and Tim just sat while Steph worked on everything. They stopped for dinner around five thirty. Sweet and sour chicken from the little family owned Chinese restaurant a block away from Tim’s apartment was a nice break from all the work. After messing around and eating for an half hour they got back to work. Tim was ready in half an hour.

“All right Timbo. I gotta hit the road but I suggest you call a taxi or Uber or something because I wouldn’t suggest driving and messing up your hair, makeup, or heels.” Steph said giving Tim a knowing look.

“Hey, just because that happened last time doesn’t mean it’ll happen this time!”

“Tim the whole left side of your face looked like you had rubbed it with wet waffles.”

“Humph,” Tim grumbled.

“Do whatever you want just look nice when you get there.” Steph waved as she retreated into her bedroom. “And remember to have fun! Also lock the door when you leave!”

Tim smiled and looked himself over in the mirror. He looked like a completely different person, which is what he was going for but still.

‘I bet I could fool even Bruce with this outfit or at least Dick.’ 

It was that thought which changed the rest of Tim’s evening drastically.

After deciding that it was probably best to call an Uber Tim selected the nicest car within a ten mile radius he could find. He ended up with a big black SUV. So not necessarily the nicest but better than the 1995 tan coop a mile away. When the car arrived he stepped in and confirmed the destination of Wayne Manor. The ride was long and uneventful due to the unruly Gotham traffic at seven in the evening. Tim watched the blocks go past slowly and the cars slower. He contemplated everything he was about to do. He need to get close enough to Councilman Sinclair to strike up a conversation and somehow warp the conversation into talking about the objective information all while maintaining his cover. This was going to be easy peasy lemon squeezy.

This was going to be difficult difficult lemon difficult. Tim’s been roaming the gala for over half an hour and has caught no sign of the councilman. He’s been making casual conversation with council members and others who know Sinclair but no one seems to have seen him or know where he was. Due to boredom and his hour of searching to no avail Tim makes and split second decision and turns abruptly towards the host of the gala. Good ole Bruce Wayne himself. As he is walking though he is bumped into my a tall man who spills his drink all over Tim’s dress.

“Oh my goodness! I am so sorry ma’am! Here let me help you!” The man holds out a cocktail napkin. “I really should have been looking where I was going I’m so sorry!”

“No it’s fine!” Tim holds his hands up as he looks up from the large stain on the front of Steph's dress. “I-“ Tim stops talking as he looks at the man’s face. With those startling blue eyes and stark contrast between his just black hair and the white streak in the front the man is easily recognized. It was Jason-fucking-Todd.

“I really am so sorry, miss! I just didn’t see you!” Tim was confused for a moment before he remembered that he at that moment was her and Jason seemed totally convinced. A small smile crossed Tim’s face and he decided this was the perfect opportunity to get back at Jason for all the stuff he’s put Tim through. All the rudeness and refusing to call him nothing other than Replacement. This was going to be fun.

“Oh no sir it really is not your fault! I should have been watching where I was going!” Tim raised his voice a little higher just to sell it. “I just- Do you know where a bathroom is? This is one of my friends dresses they lent me and I’d like to make sure it doesn’t stain!”

“Oh of course!” Jason gave Tim one of his infamous fake charming smiles. “Right this way!”

As Jason ushered Tim towards the door, Tim noticed him turn back and glance at none other than the first Robin, Dick Grayson himself. Dick, who was now in his mid twenties, was giving two thumbs up to the taller man walking beside him. Tim pretended not to notice it nor Jason’s almost unnoticeable nod in Dick’s direction. But now Tim knew that messing with Jason was about to get a lot easier since by the secret interaction it was clear Jason was going to try something. 

Tim’s suspicions were strengthened when instead of taking Tim towards the lobby to the restroom, Jason was leading Tim towards a side door which led deeper into the Manor. Tim said nothing as the exited the ballroom choosing to follow Jason wordlessly for the time being.

Jason took him down a few hallways and a flight of stairs and as they were (un)surprisingly nearing the guests rooms in the Manor Tim spoke up.

“You would think they would have made restrooms closer to the ballroom!” Tim laughed turning to Jason.

“You would think.” Was all Jason had to reply.

**Notes for the Chapter:**

> Eh... I think it’s pretty shitty but who knows maybe I’ll get better in the next bit!


End file.
